How to become a bad boss: Make the little trade-offs.

Here’s why it’s so easy to become a bad manager, even when you don’t mean to be.


I was running a leadership training a few months ago, when a CEO said this to me: “I think I know why it’s so easy to become a bad manager, even when we don’t mean to be: It’s because of the little trade-offs.”

I nodded and smiled. I knew exactly what he meant by “the little trade-offs.” I’d made so many myself as a leader, across my own career. The little trade-offs are the moments when we succumb to what feels most pressing in front of us, at the expense of what our company needs down the road to be successful. We swap “The Thing That Will Help The Team in the Long-Run” for “The Thing That Needs To Be Done Right Now.”

As a leader, we make a dozen of these little trade-offs every week (if not every day!) We negotiate in our heads: “I need to finish this critical project, so I’ll postpone my one-on-one meeting with this employee. We can talk next quarter.” Or, “I need to be heads down on selling to this new client, so I don’t have time to explain the recent company changes. We can announce them later.”

“Next quarter.” “Later.”

In the moment, the little trade-off seems like the right one make. Executing on “The Thing That Needs To Be Done Right Now” feels like the top priority. It’s what will pay the most dividends. And when it’s such a little trade-off, how much does it really matter?

Well, here’s the rub: Little trade-offs are not so little. You might make just one or two, in the beginning. But when you’re stressed, busy, and operating on tight timelines, the frequency of those little trade-offs inevitably increases. The little trade-offs you make as a leader become big trade-offs over time.

Consider these seemingly “little” trade-offs:

You choose to respond to an investor’s message within 24 hours — but don’t respond to a team members’ email or message for days (or weeks) on end.

You choose to be out on the road marketing the company’s new vision to potential customers — but don’t take the time to communicate the vision to the rest of the company.

You choose to actively ask a client for feedback and how your product can improve — but are always late to deliver an employee surveys or hold one-on-ones to solicit feedback on how the company can improve.

These little trade-offs say: “I value investors over my team. I value my potential customers over my team. I value my current customers over my team.” These are not little trade-offs. They’re big.

Over time, the little trade-offs reveal your true preferences as a leader and the basic underlying assumptions you hold. It becomes clear who and what really has a hold on you, and where your interest lies. For your team, the little trade-offs you make speaks volumes to them, more than any stirring inspirational speech or pay increase you give. It’s the little trade-offs that they’ll most remember.

No wonder it’s so easy to become a bad manager. Our little trade-offs pile up. Rather than being the exception, they become the rule.

How many more little trade-offs are you willing to make?


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The leadership tip we overlook: Knock out the small stuff

How the smallest action as a leader can have the biggest impact on employee morale and job satisfaction.


“I had no idea it mattered so much.”

A CEO said this to me about a year ago. I’d run into him at a conference. As we sat down at lunch together, he shared something that had happened to him recently…

A few months prior, he had asked his team a question through Know Your Company (they’re a happy customer!). The question was:

“Would you like a new office chair?”

The CEO initially thought the question was a little silly, to be frank. Did office chairs really matter? He doubted anything meaningful would come of the question, but he decided to ask it anyway.

Turns out, every single person in the office (they’re about a 14-person company) responded with, “Yes, I’d like a new office chair.” Not only that, but many of them wrote lengthy, in-depth responses about how unhappy their chairs were making them — how it hurt their lower backs, how it kept them from concentrating and focusing on their work.

“I was shocked,” the CEO told me. “Something I thought was so small, was actually pretty big.”

So he decided to do something about it. The following day, the CEO asked everyone to pick out their own office chairs via Amazon or another site online. The chairs got shipped to the office the next week. Everyone spent a few hours all together during one afternoon, assembling their new office chair, laughing and joking with one another.

To the CEO’s surprise, it became a bonding event. He described: “That single moment alone — getting people new offices chairs — boosted morale in the company more than anything else I’ve tried. The energy of the office has completely shifted since then.”

He continued: “I’ve spent tens of thousands of dollars on training programs and all sorts of employee engagement initiatives… and office chairs was the thing that did it?!”

The CEO couldn’t help but laugh. He never expected that acting on something so small would make such a big difference.

But it did. And it makes sense.

Taking action on something small is the single most effective way to increase morale in your company. When you do something that an employee suggests, you’re literally sending the message: “I want things to be as YOU would like them to be.” That’s powerful. Actions truly speak louder than words in this case.

It may sound obvious, but we often forget this as leaders: People share feedback because they want some form of action taken. No one is saying they’d like a new office chair just for the sake of saying it — they’d like the issue addressed somehow. Doing something (even if it is just getting new office chairs) reinforces that you’re listening as a leader, and encourages folks to speak up and be honest with you in the future.

Consider it a “quick win.” No matter how small, it makes a real difference.

Is there something small that was requested by an employee, that you haven’t gotten around to yet? Knock out the quick win.

Is there a decision that you’ve been sitting on, because you didn’t think it was that important? Knock out the quick win.

Employees value responsiveness. They’ll feel encouraged that their words led to action. That momentum will have a positive effect on morale.

Even if it’s office chairs, it’s a quick win. Knock it out.


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P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

The 3 employee benefits that have the biggest impact on team morale at work

Part of being a good leader is knowing which employee benefits to offer. According to 1,000 leaders in The Watercooler, these 3 make the biggest difference.


Four in five employees want more company benefits than a pay raise. That’s according to a 2015 survey conduced by Harris Poll.

Woof. It begs the question: Which employee benefits should you offer?

A Glassdoor study conducted in 2016 found that employees’ top-ranked company benefits were health care insurance (e.g., medical, dental), vacation/paid time off (37 percent), performance bonus (35 percent), paid sick days (32 percent), and 401(k) plan, retirement plan and/or pension (31 percent).

Today, however, benefits like health insurance and performance bonuses are seen as “givens” for more and more companies. One executive, who is a member of The Watercooler (our online leadership community), explained that having benefits like health insurance, bonuses and sick leave are more so “morale killers” if they’re not there — but not necessarily “morale boosters.”

So what are the “morale boosters” of employee benefits? Which ones truly help differentiate your company from others?

I recently posed this question to The Watercooler, our online community of almost 1,000 managers and leaders. According to them, here are the top three benefits their employees that make the biggest difference:

#1: Remote work

Remote work was by far the most frequently cited employee benefit that Watercooler members’ teams appreciated. An employee can go pick up her kids and take her to gymnastics, or head to a doctor’s appointment in the middle of the day that’s typically difficult to schedule otherwise. This flexibility matters: Best-selling author Daniel Pink talks at length in his book Drive about the importance of autonomy for people to be happy. Giving folks the flexibility to work in an environment that is best suited to them — to avoid the commute, to work from the quiet of their home at their own standing desk — might just be the reason benefits are viewed more favorably than a pure pay raise.

#2: Support for family members

Many leaders agreed how supporting your team’s family members goes a long way. One leader in The Watercooler, mentioned how his company offers a “Travel Pizza” night that’s been a huge hit with his team. They reach out to the families of employees who are on the road, and deliver pizza for the night while their loved one is away. While a seemingly small gesture, it recognizes an employee’s contributions in a meaningful way. Similarly, another Watercooler member shared how when a long-time employee’s wife slipped a disc in her back and was in a lot of pain. So his company dropped a week’s worth of frozen meals in (homemade!), and the employee only found out about it when he got home in the evening to an ecstatic wife and a warm meal.

#3: Allowances for healthy living

A good number of Watercooler members discussed how benefits that promoted employees’ health and well-being were exceedingly popular (especially when employees can choose what those exact benefits are). One manager in The Watercooler gives their employees $200 per month to spend on anything that you can reasonably argue goes to your health and well-being. One of their employees used it to cover teacher training classes for yoga, another uses it for regular massages, while another uses it for painting classes. At the end of the day, employees who feel their whole life — not just their work life — is being supported by a company is being is less likely to take time off work, and even more willing to invest in helping their team make progress toward its goals. Support their health, and you support an employee’s ability to contribute to the team.

If you’re evaluating your own company’s benefits package, consider including one (or perhaps all!) of these three benefits mentioned here. More than a pay raise, it might make the difference you’re looking for.






P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew.)

6 tips to be a better manager in the most common situations you’ll face

Whether you’re a new manager or hate delivering negative feedback, I share our most popular tips for the situations that managers most frequently encounter.


“If there’s one thing you should be doing to become a better manager, what is it?” I got asked this question recently.

My answer: It depends on on the situation 🙂

It may seem like a cop out answer, but it’s true. What you should do to be a better manager has everything to do with your personal tendencies and habits, your team’s dynamics, and what’s going on with your team in a given moment. It’s about the particular situation. Broadly recommending that you should “make decisions more quickly” or “focus on engaging your team” is unhelpful unless those recommendations are calibrated to your situation.

So I’ve compiled together below six of the most common situations managers often find themselves in, and our most popular recommendations for each:

If you’re a new manager Slow down. Build trust, first.

When you’re a new manager, it’s tempting to want to prove your worth. You want your team to know they’re in good hands. However, the best way to establish your legitimacy as a new manager is to build trust, first. Don’t dive headfirst into charting a vision or make any sweeping changes you think are needed. One of the best ways to build trust during your first team meeting is to share who you are — but more than just the surface level stuff. Your direct reports want to know: What causes do you believe in? What do you see as your greatest weaknesses? What’s your leadership philosophy? Getting to know the real you, especially during your first meeting as a manager, helps build trust. Here are some other suggestions I have for running your first meeting as a new manager and for building trust.

If you hate delivering negative feedback Say, “I’m giving you this feedback because I want you to succeed.”

You cringe at the thought of having to tell a direct report something they might not want to hear. However, if you focus on why you’re giving the person this feedback — that you care about them, the company, etc — it shows that you’re trying to help, not hurt, them. Here are 19 phrases that can help you share critical feedback even if you have a strong aversion to the process.

If you’re not sure how to recognize employees Share a customer review.

Employee recognition is all the rage these days — but we can often forget how to sincerely give employees that recognition. When delivering praise, it can be tempting to offer a gift card or some other incentive. But there are few things as genuine and gratifying for an employee than sharing a positive customer review. That’s not the only way though: Here are 8 ideas for how you show appreciation toward your team in a meaningful way.

If you notice your team hanging on to your every word Say, “This is not urgent.”

As the boss, your words can be taken seriously — sometimes, too seriously. The best way to mitigate this is to explicitly tell people that your word is not the word of god. One way to do this is to say, “This is not urgent,” so folks don’t prioritize things they shouldn’t. You can learn about why this happens and another phrase to use to diffuse your word as a leader here.

If you tend to get defensive when receiving feedback Assume positive intent.

Your reaction to feedback sets the tone in a team for how receptive you are to feedback. So if you react defensively, you discourage your team from ever bringing up feedback to you again. To ease your own defensive tendencies, take a moment to assume that the other person has positive intentions. They’re not out to get you — they just want something in the company to change. Here are four other ways to not get defensive while receiving feedback as a manager.

If you’re struggling to get honest feedback Ask for advice, instead of feedback.

Asking someone for their guidance shows that you trust their expertise or knowledge. The word “feedback” is loaded with emotional baggage — it’s negative, formal, and forced. So while employees are hesitant to give feedback, who doesn’t love to give advice? Switching out that one word can open up lines of communication you might not have otherwise had.


Any of these situations feel familiar? If so, I hope taking the one small step I recommended puts you in better footing as a manager. Remember, you don’t need to start changing a bunch of things, all at once. Your progress as a manager can begin by making one change specific to your situation.






P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew.)

How do you measure company culture? You can’t. But you can do this instead.

Culture isn’t meant to be measured. Here’s why, and what you should measure instead.


“How do you measure company culture?”

Someone asked me this recently.

My answer: You can’t. And you don’t want to.

Why? Because culture, technically defined, is the artifacts, espoused values and beliefs, and basic underlying assumptions that people have. And that can’t be measured quantitatively.

Nor is it the point of culture, to begin with.

Culture is an organization’s compass for behavior. It’s what people use to decide what actions are acceptable, and what are not. At one company, it guides people to publicly report a mistake. At another company, it nudges people to brush a similar mistake under the rug.

To say you want to measure culture is like saying you want to measure a compass. You could pick it up and say, “Hmm, let me rate the shininess of this compass, or weigh how heavy it is.” But, really, what you care about is if the compass points you to where you want to go. Measuring the compass itself doesn’t do you much good.

The distinction is important. Because if you don’t see culture as a lever that influences what you’re trying to accomplish as a team, and instead as the thing itself you’re trying to maintain, you lose sight of culture’s power in the first place: Culture helps a group of people get what they want done, done.

As a result, what you can measure are the outputs of culture. The observable behaviors and outcomes you want to see as the consequences of your culture.

Possibly the most important output to gauge is progress. Ask your team, “Do you feel like you’re making meaningful progress every day?” Studies show how progress, more than anything, influences employee motivation.

This means defining what “progress” looks like on a day-to-day basis. Is it the speed by which things are happening? Is it the quality of the work being produced? Is it the number of people you’re helping because your work product exists?

It could also mean asking questions to your company about how helpful their manager is in supporting them to make progress, or how frequently they encounter frustrating obstacles in a given week.

In short: If you want to measure culture, start with clearly defining what the outputs of a successful, healthy culture looks like for you — and get super specific. Then, figure out what questions you can ask employees on a regular basis to gauge for that.

Don’t measure the compass, itself.






P.S.: If you enjoyed this piece, please feel free to share + give it 👏 so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

The 3 phrases you’re saying that trigger employee disengagement

Stop saying these words — you’re wearing your employees thin.


You’re doing it again. You don’t mean to, but it’s happening: Your words are damaging your team. Small, off-hand remarks color how an employee thinks you value their work. Comments seemingly innocuous to you are in fact infuriating to your team.

You may have started to notice this. When you praise an employee, your compliment is met with an empty stare. When you announce a decision at a meeting, the reaction is silent agreement… or perhaps, silent fuming.

Your words aren’t helping. They’re hurting.

As demoralizing as it might be to recognize this, there’s an upside. Improving employee engagement can be as straightforward as changing what you’re saying to your team. It doesn’t have to be about investing thousands of dollars in a new employee benefits program, or bringing in an external consultant to write a custom employee engagement survey. To boost your team’s engagement, you can simply stop saying certain phrases.

Here are three phrases I’ve been a perpetrator of saying — and that I’m sure you have too – that can cause an employee to be disengaged:

“Not now”

You say this when a new idea is offered. Not every time, but half of the time. I get it. You can’t implement every idea, and it’s tiring to field new initiatives during a meeting when you’re already short on resources. But consider how dismissive the phrase “not now” can be, when an employee goes on a limb to offer a well thought-out idea. Snuff out a suggestion and you snuff out an employee’s motivation to bring it up the next time around.

While you can’t implement every idea, your knee jerk reaction doesn’t have to be “not now” each time. Instead, say specifically when you’d like to reconsider the idea (e.g., “Can we revisit this next month?). Or say honestly share why you don’t think it’s a good idea, all together (e.g., “Here’s why I don’t we should pursue this…”). Your team will appreciate your candor, instead of feeling strung along that maybe this will happen in the future, maybe it won’t.

In the end, remember that suggestions are a harbinger of employee engagement. Your team cares enough to want to make things better. Greet these suggestions with enthusiasm, curiosity, and a genuine desire to explore them.

“Good job”

An employee completes a project and we instinctively say, “Good job.” Ron Carucci in Harvard Business Review calls this “drive-by praise” We pop our heads into their office and briefly say “thanks,” or send a quick 👍 on Slack. Yes, it’s better than saying nothing, but employees want (and deserve!) more. They want specifics on how they can improve, and feedback on what they did well.

Uttering “good job” doesn’t show that you understand all the work they did, and doesn’t help them do better next time. Don’t wait for performance reviews to give detailed feedback, either. Take a few minutes every week or two to provide feedback and sincere, specific praise for what you think they’re doing well. For example, you could say, “I learned a lot from you by watching how you interacted with that upset client with grace and steadfastness.” Compare those words to merely saying, “Good job with that angry client.” If you’re curious for more ideas for ways to express gratitude in words sincerely, read this.

“ASAP”

We lean heavily on these four letters, as managers. Fires are burning everywhere, so saying “ASAP” communicates urgency to our team. But urgency is a spectrum — and ASAP includes no nuance for where on that spectrum something actually is. As a result, “ASAP” creates confusion for our employees: “Is it actually urgent, or somewhat urgent?” When employees feel constrained on time unnecessarily, they’re frazzled — and their work and morale suffer because of it.

Rather than relying on these four letters to communicate urgency, first consider what degree of urgency is this? For example: “This is highly urgent and needs to be turned around in the next 24 hours,” or “This is fairly urgent and should be prioritized over most tasks, but can be finished by the end of the week.” Be conscious that the amount of time you give someone to complete a deliverable affects their level of engagement. Gallup in fact found that “when employees say they often or always have enough time to do all of their work, they are 70% less likely to experience high burnout.”


Saying these phrases on occasion are harmless. It’s the repetition of them over time that inflicts harm. Like a tire driving over a road, the more pressure applied and the more times travelled, the more you wear the ground underneath it.

Better to just stop driving on those roads. Better to just stop saying these phrases.






P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew.)

Stickers vs. Words: 8 ways to give employee recognition sincerely

I’m tired of gimmicky ways to praise your team. Here’s how to commend your team for a job well done, meaningfully.


My third grade teacher Ms. Mullens had a bulletin board of star stickers in her classroom. On the board, she’d place a star sticker next to your name if you’d cleaned out your cubby, tucked in your chair, and turned in your homework on time.

I liked those star stickers. But what I appreciated even more was what Ms. Mullins wrote on my report card: “Claire is a conscientious, caring individual…

I still remember that decades later. Her words mattered, not her stickers.

When it comes to employee recognition, we seem to have forgotten this. These days, we care about the stickers — not the the words.

Rocket ship emojis in the Slack “kudos” channel, employee recognition software with “badges,” and Amazon gift cards awarded at all-hands meetings — this is the new norm for CEOs and managers who thank their employees. Now I love a perfectly-placed, underutilized emoji (and Amazon gift card!) as much as anyone. But some of the most meaningful moments of my career have not been because someone gave me a thumbs-up badge. I’ve felt most valued when I did one small thing that really helped someone I worked with, and that person let me know in a sincere way.

Employee recognition is about saying something, and meaning it. If a heart emoji or a free lunch are the only ways you say “thank you” or “good job” in your company — you’re missing the point. If you want to say something sincerely, say it with words.

We rely on stickers, gadgets and trinkets to express our gratitude because, often times, we don’t know what to say, how to say it, or when to say it.

So I asked our leadership community of 750+ managers at The Watercooler what advice they had for managers who struggle to give praise in a sincere way. Here’s what they had to say:

#1: Don’t force it.

Praise is useful for encouraging your team — but it should be organic. If you find yourself struggling to come up with praise for an employee, pass on it this time around. Better to not say anything at all than to say something you don’t 100% believe is true.

#2: Share a customer review.

If you find it hard or awkward to let an employee know how they’re doing, try sharing feedback from a happy customer. One Watercooler member admitted: “Frankly, it makes praise easier to give and more genuine when it comes from customers.”

#3: Focus on recognizing individuals, not just teams.

As managers, our default is to “thank the sales team” or “thank the design team.” Yet, if applied too broadly, the benefits of that praise can stagnate. Studies have shown individual-based recognition systems tend to be more effective than team-based recognition systems (particularly in Western countries).

#4: Remove the buzzwords.

“You’re a rock star who’s killing it.” Yuck. Anytime you use a trite phrase, you erode the sincerity within your comment. Don’t depend on hyperbole to communicate your praise. Take a moment to be specific. Say what you mean.

#5: Praise people during one-on-one meetings.

There is nothing more sincere than commending someone face-to-face. They can hear your tone, read your body language, and look you in the eye. In these settings, you can also go into greater of detail why you value their work, and the impact of this person’s contributions to the company.

#6: Don’t be afraid to praise publicly, in front of everyone.

When you’re in a group, you can highlight and publicly praise individuals who have made progress since your last meeting. This helps establish what “good work” looks like to the entire team, and inspires other team members to step up. In fact, studies show that other team members benefit when a top performer is recognized (this is known as “recognition spillover effects.”)

#7: Make sure praise comes from peers , not just managers.

Encourage your team to praise one another. Getting recognition from you as a manager matters, but it’s also helpful to know peers appreciate hard work. One Watercooler member offered an example of a weekly tradition where people take a few minutes out of their day to give praise to their peers. “It’s optional… Not everybody gives and gets thank you’s every week, which keeps it from feeling forced or inauthentic.”

#8: Use your stickers sparingly.

Tangible gifts can backfire. A 2009 global survey conducted by McKinsey observed that non-cash incentives are more effective than cash incentives — including performance-based cash bonuses. And, they can offend some people who find them transactional. In this situation, it’s wise to ask people what they prefer on a individual basis. Also be wary that a “kudos” system in a digital communication channel (e.g. Slack) can come across as disingenuous for some teams. Ask your team if they’d enjoy it, or test it out before committing fully.

Not sure what specific words you should use when giving praise?

If you’re stuck on the words themselves, here are some ideas Watercooler members shared for things to say when you’re not sure how to praise people:

  • I like the way you’ve been showing up lately. I don’t care about the mistakes; you already know what they are. I appreciate how you’ve been taking accountability for them.
  • Thanks for helping me with X. I had no idea how to execute all of it, and I would have been up a creek without you.
  • You taught me something I didn’t know today.”
  • You’re making this job so much easier for me lately.”

There are, of course, more than these ways to deliver recognition for a job well done. The most important piece — no matter how you decide to deliver praise — is not to get lazy. Don’t use stickers. Use your words. And mean ‘em.






P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew.)

How can you tell if you have a disengaged employee? Ask these 11 questions.

Employee motivation isn’t as mystifying as it should be. Ask these questions to get to the bottom of it.


“What really motivates employees?” A CEO asked me this recently, quite skeptical of the deluge of books and articles on what influences employee engagement and performance.

It’s managers! It’s career opportunities! It’s learning and development! It’s employee recognition! It’s all of the above!

What “the experts” say is dizzying. The truth is simpler.

Research shows that employee motivation boils down to one thing: Progress. A 2010 study published in Harvard Business Review describes how making progress on meaningful work is the number one indicator of employee engagement.

When employees make headway toward a significant goal, overcome obstacles in a reasonable timeframe, and feel supported in their work, their motivation is the strongest. When they feel their wheels are spinning, run into preventable roadblocks, or notice the end-goal is constantly changing, their motivation wanes.

Given this, if there’s only one thing you should be focused on as a manager, it’s progress. You want to be relentless about discerning, “Are employees making progress on meaningful work every day?” With limited time and competing priorities, you don’t have to make employee engagement more complicated than this. 
 
To best distinguish how your employees feel about the progress they’re making, I’ve pulled together 11 questions from the data we’ve collected through Know Your Company over the past four years, specifically designed to tune into an employee’s sense of progress.

You may be wondering, “Why can’t I just ask my team, outright, ‘Do you feel like you’re making meaningful progress on the work you’re doing?’” Absolutely, you can. And you should. But pose that question enough times, over time, and fatigue sets in. You’ll notice your employees starting to answer “Yes” out of knee-jerk reaction, not genuine reflection… or, to just to get you off their backs.

Instead, these questions below will bring into your view invaluable insights that an employee might not always divulge: The root cause of why they feel the project is quicksand, who on their team is the pain-in-the-ass nitpicker causing unnecessary friction, and what you can do about it.

Here are the 11 questions to figure out if employees feel they’re making meaningful progress — and what we’ve found most employees say in response:

#1: Is there anything you worked on recently that you wish you could do over?

Dissatisfaction should always cause your ears to perk up — and this question is particularly effective at unearthing it. You’ll learn if an employee was dissatisfied with the outcome of a project because of team dynamics, or because it was rushed, or because there wasn’t enough direction given. Either way, the answer to this question will point to how you can better support an employee on certain projects. Notably, 67% of employees who we asked this question to through Know Your Company said, “Yes, there’s something I wish I could do over” (877 employees responded across 137 companies).

#2: Is anything holding you back from doing the best work you can do right now?

To uncover what blockers someone is facing, we tend to rely on stock questions like, “What challenges are you facing?” or “Are you struggling with anything right now?” While there’s nothing inherently wrong with those questions, because these questions tend to be overused, you may not always get the honest answers you’re looking for. Rather, asking what is holding them back helps you triangulate more specific challenges an employee faces, while avoiding routine answers. In fact, we found 58% of employees said, “Yes, something is holding me back from doing my best work” (1,027 employees responded across 124 companies) when asked through Know Your Company.

#3: Do you feel like customers directly benefited from the work you did this week?

Progress feels most meaningful when you can see the impact that you’re making. So knowing whether or not an employee feels like customers benefited from their work is a useful proxy for progress. The good news too is that when asked, we’ve found that 90% of employees say, “Yes, I feel like customers directly benefited from the work I did this week” (1,114 employees responded across 134 companies).

#4: Do you wish you could be working on a different project right now?

Affinity toward a project can signal an employee’s sense of progress. Someone may purely be intrinsically disinterested in the subject matter of the project, while others could be sick of tolerating bad blood on a team, or an employee might feel the work you assigned to them is a mismatch of skill. In all situations, there’s more to poke around and learn more — and this question helps lay that bare. Nearly a third of employees we surveyed (29%) said they wish they could be working on a different project right now (1,942 employees responded across 148 companies).

#5: As a company, do you think we’re behind the curve on anything in particular?

For employees to feel they are making progress, they need to feel the company as a whole is making progress. This question reveals that. It’s disheartening as an employee to pour their best work into their team, but feel the company doesn’t prioritize areas that it should be ahead in. Perhaps most fascinating is that the majority of employees say, “Yes” to this question: 65% of employees think their company is behind the curve on something in particular (1,267 employees responded across 190 companies).

#6: Do you feel like you’re spread too thin right now?

“Overworked, scattered, drained” — these are all hints that an employee doesn’t feel she’s making sufficient progress. Not to mention, overworked employees report more health problems, and as a direct consequence are less productive and use more sick days. Yet, it’s rare an employee will come up and tell you outright: “I’m overworked.” However, asking if someone feels “spread too thin” is a much more palatable to answer. It doesn’t have an employee feeling guilty or wondering if their work ethic will be in question. We found that 36% of employees (slightly more than a third!) said they feel spread too thin right now (2,173 people responded across 179 companies).

#7: Do you think we’re doing our best work right now?

Ask this question to get an idea of if your employee thinks the team is holding itself to a high enough standard. If she feels good about the quality of the work, then you can likely deduce she feel good about the progress of work being made. Encouragingly, we found 59% of employees surveyed said, “Yes, I feel the company or team is doing the best work right now” (1,073 employees responded across 160 companies).

#8: Is there an area outside your current role where you feel you could be contributing?

When an employee feels like they could be doing more, it’s probable that she is discontent with the rate of progress that she could be making in her current role. Ask this question to recognize out what other projects, skills, or knowledge domains an employee wants to dive into — or if there’s more growth opportunities you could provide them with in her current role. This will help you figure out how to ensure they’re motivated. Take notice that an overwhelming majority — 76% of employees — surveyed said, “Yes, there’s an area outside my current role I feel I could be contributing” (814 employees responded across 135 companies).

#9: Are you being forced to do something that you think is a waste of time?

Nothing feels more depleting for someone’s motivation than wasting time. Asking this question will draw your attention to the excess baggage weighing your team down, or pointless bottlenecks holding up your team. We found that 25% employees said, “Yes, they’re being forced to do something that is a waste of time” — which is not insignificant (852 employees responded across 113 companies). Ask this question to accelerate progress for your employees.

#10: Are you working on a project that you feel like has gone on too long?

When a project drags out forever, an employee’s motivation to see it through naturally diminishes. You’ve most-likely felt this way in your own career, feeling dejected or peeved when a project stalls for a reason outside your control. Now as a manager, you’ll want to detect within your own team who is feeling this way. We discovered a surprisingly high number — 37% of employees — feel that they were working on a project that had gone on too long (615 employees responded across 94 companies). Identify which projects those are, so you can help remove barriers to progress.

#11: Is there any red tape you’d like to cut at the company?

Policies that are no longer necessary, procedures that you’ve even forgotten were there in the first place — this all slow down the rate of progress. Fortunately, as a manager, it’s within your scope to trim this fat. Remember how freeing it is for yourself to operate without impractical constraints. And, keep in mind that 24% of employees said “Yes, there is red tape I’d like to cut at the company” — so there is ample opportunity for you to slash the red tape that is preventing your team’s progress (591 employees responded across 105 companies).


Here’s the best part of all of this: 80% of the answers will expose things that you have control over. You have control over what the policies in the company are, what projects are assigned to which employees and when, the goals of a project, the deadlines set, the amount of support that’s being given, and the sense of direction.

And for the things you don’t have control over —a difficult client you can’t fire right away, or an incompetent team executive who doesn’t report to you— knowing the impediments to progress can inform your decisions to a clearer path of progress.

Employee engagement isn’t as mystifying as it should be. Progress is the linchpin. Asking these questions can help you secure it.






P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew.)

Watch our lessons for leaders: The Heartbeat Interview ❤️ with Aynn Collins, Director of Talent…

An expert on employer brand and recruiting at the 900+ person company, Mailchimp, Aynn shares what she wishes she learned earlier as a leader around failure and vulnerability.

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Aynn Collins, Director of Talent Strategy at MailChimp. Watch & read what she has to say here…

Claire: Hi, everyone. I’m Claire Lew, and I’m the CEO of Know Your Company, and today, I am so excited to have with me, Aynn Collins, who is the Director of Talent Strategy at MailChimp, possibly one of my favorite companies and a lot of people’s favorite company. I happened to meet Aynn at a conference this past year in Austin, and it was amazing to hear, first of all, what her role is in the organization.

As the Director of Talent Strategy, with MailChimp now being 900 people and counting, she manages employer brand and the employee experience. I’ll let her talk a little bit about that, but really excited to have her here and to ask her this one question about leadership. Aynn, thanks again for joining me.

Aynn: Thank you for having me, Claire. I enjoyed meeting you at Culturati Conference as well, so I’m flattered you wanted to talk to me.

Claire: Oh my gosh. Of course. All right, Aynn. I’ve got this one question for you about leadership, and it’s if there’s something you wish you would have learned earlier as a leader, what would you say that is?

Aynn: That’s a really good question, so kind of talking to my to my younger self about leadership, it sounds like you’re asking me. That’s funny you asked me that because here at MailChimp, I end up talking with a lot of employees here about things I learned early in my career, whether it be leadership management style, feedback, what-have-you.

I think I would tell my younger self to really embrace failure. You learn much more from a single defeat than from a thousand victories.

Obviously, nobody’s excited about failure or not meeting a goal, but not sweeping that under the rug and talking about it, so just really embracing failure and understanding how you learn and grow from those failures, I think is what I would tell people to learn early in their career. They can own failures, talk about them, debrief with your team on, even if the whole project wasn’t a failure, what that have done better, and not try to just make everything shiny and pretty. Because we know business and leadership is not always perfect, and shiny, and pretty. We all have failures all the time personally and professionally, and I think that’s something that I really encourage people to talk about.

In fact, yes we introduced a really cool program here last year. Part of my role is employer brand, so really amplifying what makes MailChimp a special place to work to the outside world.

I think the key to an authentic employer brand is making sure that you’re really telling the true story, like don’t make it too perfect. Make it who you are.

The best way you do that is to get employees out in the wild talking about MailChimp, whether it be technical talks or speaking about our culture or just being an ambassador when you’re out a conference or out in the wild.


We have this really cool speaker training program at MailChimp, and one of the things we did last year is introduce an internal program called Fail Tips. It’s basically a lunch and learn format where six to eight employees do a five-minute or less talk on a personal or professional failure. You wouldn’t believe the waiting list I have for people that are willing to talk about their failures and how they learned and grew from that. Yeah, that’s definitely something I think we’re doing well at MailChimp is looking at how we can do things better and not sweeping the things that didn’t go well under the rug.

Claire: Absolutely. I love this topic of failure when it comes to leadership because I think you talk to some entrepreneurs and some leaders, and they’ll tell you that they actually don’t really even believe in the word failure and that there’s no real failures but all they really are really expensive mistakes. A lot of leaders actually even reframe the way they look at failure as just saying, “Well, no. This is just how you actually learn.” Failure has just such a negative connotation, and so I love your emphasis on this.

I’m curious, Aynn, so for you personally in your journey and career as you become a leader, when did this click for you? Did something happen or did you watch something unfold or did you experience something where you went, “Oh my gosh, I need to wake up and make sure that I’m not sort of sweeping failures under the rug”? When did it really hit you how important this was?

Aynn: I’m not sure there was a specific “aha” moment. You’re still feeling the pain of the failure about four or five different things but I can remember, at a different company, this is not at MailChimp, where I was head of recruiting. We had to hire. We were hiring a leader in a role that was sort of struggling. It was a young startup, and we felt like we needed somebody with a stronger personality to really motivate people. We interviewed and hired a woman that had a very strong personality that, at the time, seemed like the fix. Once we got her in and on-boarded, it became apparent quickly that her style was just too different than our cultures and that she wasn’t listening to that culture and sort of adjusting her style, and instead of motivating the employees, which is what we really wanted her to do, she was demotivating.

Our executive team at that company made a really good quick decision to go ahead and terminate that relationship, and then talked to that team about our failure to them. I think being very, very clear about we made a mistake and this is what we’re going to do differently in the next hire, we’re going to listen to your feedback because there was some concern from this person’s direct reports during the hiring process that it was too different than our style, and we glossed over that. They were very appreciative of that.

I always feel like, that even here at MailChimp, when we push something too hard and didn’t get the right feedback, when we stop and listen and say, “Wow, you were right. We really should have asked you before we implemented this policy. Let’s change it,” you get this level of forgiveness and trust from your fellow employees when you admit that failure and adjust that you just can’t buy. That’s probably the best way we’ve built trust here and in other roles is by admitting our shortcomings and adjusting quickly.

There’s a story of many years ago where a hiring failure sort of taught me a lot. I actually, in between that company and coming to work for MailChimp, I had a small business failure, so I started a line of clothing for mothers. It was clothing and fun accessories. It was going very well, and then 2008 happened. I decided to close that business. It was very painful because I had really aligned myself with that brand. I was very proud of that, but I made a tough decision to quickly get out of that, and that was that. It was really hard for me. It’s still sometimes hard for me to even see references to that part of my life and be like, “Oh, that was so …” but what I realized actually when we did this fail tips program, and I bared my soul to the MailChimp employees and told them how hard that was is that, well, it led me to MailChimp.

MailChimp’s vision is to empower small businesses. It’s to empower the underdog, which in our definition is small businesses, so I feel that pain. I can empathize with small businesses now, and even though my role is not directly product focused, it makes me really aligned with the company I love. If I hadn’t had that small business failure, I wouldn’t know the things small business owners have to do every day just to keep the lights on. That failure led me to MailChimp. I know I’ll have more failures, right? I think I’m that more resilient. It made me that much more humble. It makes you think. It makes you get more input and feedback before you make decisions.

I am not a failure but I embrace failure.

Claire: Absolutely. I mean, I think both those stories are sort of amazing windows into understanding how unexpectedly, failure leads you to your point of greater feedback, greater insights, better decisions, and then also just ultimately a better path for what you want to be doing. In the moment, it never feels like that. Let’s be clear so that everyone who’s watching, it never feels like that in the moment.

Aynn: It feels terrible.

Claire: Yeah, so my question to you, Aynn, is then for current leaders and aspiring leaders who are watching this and who struggle with being vulnerable, who struggle with … who maybe, I mean let’s be real. They’re in a high-pressure situation. There’s maybe a lot of money on the line. There’s a ton of competitors. Everything needs to be moving really quickly. They’re trying to attract and retain the best talent. How can you afford to be admitting all the time all your mistakes? What would you say to anyone who’s watching who’s skeptical about sort of doing this in practice?

In theory, it’s great. It sounds good. Maybe doing it here and there once in a while is good, but you’re talking, I think about being a lot more rigorous about admitting shortcomings and failures. What would you say to anyone who might be sort of skeptical about doing this in practice?


Aynn: Yeah. I think with anything, you have to apply sparingly. Your team needs to have confidence in you, and we certainly don’t have to show every bit of vulnerability but vulnerability goes so far in leadership, I think. I think what I found is when I have leaders that I work with or support do admit failures or shortcomings or missteps, sometimes it’s just a misstep, it’s not a full failure, that you really get this loyalty from your employees that, again, I think I said earlier, you can’t buy or you can’t teach. It really rallies them to get behind you and help you and the entire organization not let that happen again because failures should not be repeat failures.

You should learn from every failure and think about how you’re not going to let that specific failure happen again. If you have confidence in saying, “This is where we screwed things up. Here’s how we’re not going to do it again,” I think you get the most amazing engagement with the people you manage and lead.

Claire: Absolutely. I think as leaders, we can be often hyper self-critical so to sort of admit every single small dent in the porcelain isn’t what we’re going for here, but to your point, I think one of my personal greatest sort of moments of progress that I’ve made as a leader is I remember we made a really big mistake with Know Your Company maybe three or so years ago with our code base. We accidentally revealed all these private answers that people weren’t supposed to see. It was this huge mistake, and it affected hundreds of CEOs.

There were two options. We could either tell folks that this happened because people weren’t aware — no one noticed it. Or, we could just not say anything and just fix it and move on.

We had a really big debate about this with our team internally about what we should do. I remember what we were faced with was, well, do we admit it publicly or just, yeah, is it fine and should we just gloss over it? What I ended up doing is I remember calling Jason Fried who’s the CEO of Basecamp, and he sits on our board. I remember calling Jason and telling him the situation. All he said is he asked me this question, Aynn, which he said, “What kind of company do you want to be?” He said, “I love situations like this because it forces you to ask that question.”

The minute he said that, that’s when I knew what I was going to do. I decided to be really transparent about what happened. I told all our customers exactly what happened, and the response was fascinating. I braced myself expecting it to be angry, and to your point, it was the exact opposite. People were so appreciative. They said, “Claire, thank you so much. Mistakes are made while you’re doing work. Don’t even worry about it.” It created this greater sense of loyalty.

Almost what that story to me makes me think about is it’s not just asking the question what kind of company do you want to be, but it’s also asking the question what kind of leader do you want to be. To your point, Aynn, when you’re in those moments of, “Oh, should I say something or should I not?” asking that question can hopefully help people decide whether or not to divulge something, so thank you for, yeah, for sharing that.


Aynn: Yeah. I think that’s a great story, I always tell I have two teenage daughters, and I tell them a lot. I’m sure they get annoyed by it.

I always say, “Don’t just be good on paper. Be good in real life.”

That is an example of being good in real life. I think people trust you. I mean, your customers probably have this greater sense of trust with Know Your Company when you’re going to tell them something like that.

Claire: Yes, absolutely.

Aynn: It’s such a great story.

Claire: Well, thank you. You fall flat on your face and you learn from it. One last question for you here, Aynn, because you are such an expert around thinking about the employer brand and how you, to your point, take what already exists within an organization and expose that outward.

When it comes to being vulnerable, when it comes to failure or just in general, what should leaders who are watching this who unfortunately don’t have you on their team and a director of talent strategy on their team, what are some things that they should be thinking about, small things, big things, to create an employer brand that really reflects what their true experience as employees are?

Aynn: I’ve been in this role two years at MailChimp, and I handle things from what does our jobs page look like to from a social perspective, how do we show what life at MailChimp is like, to how do we show up at conferences. For instance, we are a huge fan of the Grace Hopper Conference. It’s all female engineers once a year. How do we show up there authentically and really support, not just hiring people but the community? MailChimp’s very into community and supporting community side of things, and how do you do that in a way that attracts people that would be a great cultural compliment to MailChimp but that is true to who you really are?

Knowing your company. There’s a little pitch for you. Really understanding what your values and vision and mission are and making sure that’s woven into everything you’re putting out there about your employer brand. Really, I think the mistake a lot of companies make is making it glossier and prettier and idealistic like what they want to be.

I think it’s much better to put a great realistic view of what it’s like and how people get here, decide to join you and buy in that it’s actually much better than they even thought and that you really are living true to those things.

Not pumping things up too much, not selling perks and things that aren’t that important to your culture but really selling like, for us, it’s that connection with a small business owner. It’s being really engaged in community. It’s giving employees impactful things to work on. It’s not the ping-pong table because we have that. It’s not the benefits that we have are great. It’s really the type of work and the type of people, and the engagement you’re going to get here.

We constantly ask new hires. We have a great onboarding program. We constantly ask them like what brought you here, and what surprised you now that you’ve been here for a month? We get great answers. Sometimes like, “You know, I kind of thought I’d be working on this, and once I got here, I figured out this is how you do things.” We love it when an employee feels comfortable enough after 30 days to say, “It was not quite what I thought. Maybe you shouldn’t put this out there about yourself.”

Claire: Yeah.


Aynn: Talk to your new employees. You’ll get a great feel how your, what your employer brand is like if you get them in the first week and then say three months later to say, “Are aligned to what we’re putting out there?

Claire: Right. No, I love that asking that question two to three months later of what surprised you now that you’ve been here. That really uncovers what’s the disparity between your perception of the company and then the reality and then doubling down on, okay, what’s real. I think that’s immensely helpful. Well, Aynn, thank you so much.

Aynn: Yes.

Claire: For your thoughts. I’m sorry. I kind of cut you off there.

Aynn: No. No. I was going to say like I think especially today when so many are so focused on diversity and inclusion, and especially the inclusion side of things, that’s really important, your brand. Did people feel like they’re part of the story when they get here?

Claire: Absolutely. Absolutely. Thank you so, so much for everything you shared. It’s so helpful to think about and rethink failure, and make sure that we’re prioritizing how we talk about that. Then, so many great insights about making sure that our brands as companies are true, and not just what we want them to be but are real so thank you so much again, Aynn. We so appreciate it.

Aynn: You’re so welcome. Thanks for having me.



Enjoy this interview with Aynn? Check out all our Heartbeat interviews with leaders…


And, take a peek at some of our other resources we offer leaders…



P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks😄 (And you can always say hi at @clairejlew.)

Quiz: Do you have these leadership blindspots?

A short 3-question quiz to give your team so you can avoid common leadership mistakes.


Feel that? It’s your faint intuition that, as a leader, you’re not hearing the full truth. No one seems to tell you the complete story when someone decides to leaves. No one breathes a word about any leadership mistakes you might be making. As a leader, you feel you’re constantly the last to know something .

You’re right. You don’t know everything as a leader. Naturally, you have blindspots. And, naturally, it can be daunting to seek these blindspots out. What we don’t know is terrifying.

To uncover these blindspots in the most painless, least-overwhelming way possible, I’m sharing a short 3-question quiz you can ask your team. Because it’s just three questions, it won’t feel like you’re asking them to formally evaluate you. And because of the questions themselves, it’ll help you identify specifically if you have any of the three most common leadership blindspots we’ve found.

Below, I share the questions you should ask to uncover your blindspots, the data behind it, why it matters, and what you can do about the blindspot itself.

Question #1:

Do feel there’s anything holding you from doing your best work right now?”

What most leaders find: 58% of employees say, “Yes, something is holding me back from doing my best work right now” (according to 1,027 employees we surveyed across 144 different companies through Know Your Company).

Why it matters: Stifled employees can mean increased turnover. When employees are stifled and disengaged they are more likely to leave a job for a 20% pay increase.

What you can do about it: Offer meaningful incentives beyond a paycheck, such as professional development opportunities.

Question #2:

“Do you want more feedback about your performance?”

What most leaders find: 81% of employees say, “Yes, I want more feedback about my performance” (according to 1,747 employees we surveyed across 172 different companies through Know Your Company).

Why it matters: Regular, helpful feedback leads to more engaged employees. Studies have shown — leaders who give honest feedback are three times more engaged than those who don’t.

What you can do about it: Offer honest, consistent guidance to employees (and not in the form of performance reviews). Be sure to open yourself up to feedback from your team, as well.

Question #3:

Do you feel the company is behind the curve on anything in particular?”

What most leaders find: 65% of employees say, “Yes, I think we’re behind the curve on something in particular” (according to 1,267 employees we surveyed across 190 companies through Know Your Company).

Why it matters: Your team can provide a wealth of ideas. In fact, according to a national 2010 Cornell study, 20% of employees actively withhold an idea or a suggestion about a problem or making improvements.

What you can do about it: Don’t kill ideas too quickly. Encourage employees to write down ideas that challenge the status quo, offer “out-there” ideas yourself, and judiciously and rigorously evaluate them.


Ask these three question to your team, and compare what answers you receive with the percentages I shared from what other leaders have experienced. How do you seem to be fairing? Anything surprise you? And most importantly, what small steps can you take to act on the new information that you now know?

Don’t be afraid to shine a light on these blindspots. As Louis Brandeis was once quoted, “Sunlight is the best disinfectant.”


Find these questions helpful? I teach this technique around uncovering your leadership blindspots, giving feedback, receiving feedback and more, in our custom workshop, “The Feedback Loop.” If you’re interested in learning these skills firsthand through our workshop, give me a shout 🙋🏻





P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew.)